In recent years, an aging demographic majority in the Western world has come to the attention of the game industry. The recently released “brain-training” games target this population, and research investigating gameplay experience of the elderly using this game form is lacking. This study employs a 2×2 mixed factorial design (age group: young and old×game form: paper and Nintendo DS) to investigate effects of age and game form on usability, self-assessment, and gameplay experience in a supervised field study. Effectiveness was evaluated in task completion time, efficiency as error rate, together with self-assessment measures (arousal, pleasure, dominance) and game experience (challenge, flow, competence, tension, positive and negative affect). Results indicate players, regardless of age, are more effective and efficient using pen-and-paper than using a Nintendo DS console. However, the game is more arousing and induces a heightened sense of flow in digital form for gamers of all ages. Logic problem–solving challenges within digital games may be associated with positive feelings for the elderly but with negative feelings for the young. Thus, digital logic-training games may provide positive gameplay experience for an aging Western civilization.